bexarotene   Click here for help

GtoPdb Ligand ID: 2807

Synonyms: LGD1069 | Targretin® | Targrexin®
Approved drug PDB Ligand
bexarotene is an approved drug (FDA (1999), EMA (2001))
Compound class: Synthetic organic
Comment: Bexarotene is a retinoid that selectively activates retinoid X receptors (RXRs), and is used for its antineoplastic action.
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View more information in the IUPHAR Pharmacology Education Project: bexarotene

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 37.3
Molecular weight 348.21
XLogP 8.16
No. Lipinski's rules broken 1
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Canonical SMILES Cc1cc2c(cc1C(=C)c1ccc(cc1)C(=O)O)C(C)(C)CCC2(C)C
Isomeric SMILES Cc1cc2c(cc1C(=C)c1ccc(cc1)C(=O)O)C(C)(C)CCC2(C)C
InChI InChI=1S/C24H28O2/c1-15-13-20-21(24(5,6)12-11-23(20,3)4)14-19(15)16(2)17-7-9-18(10-8-17)22(25)26/h7-10,13-14H,2,11-12H2,1,3-6H3,(H,25,26)
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Retinoid X receptor-β Primary target of this compound Hs Agonist Agonist 7.7 pIC50 - 1-2,4
pIC50 7.7 [1-2,4]
Retinoid X receptor-γ Primary target of this compound Hs Agonist Agonist 7.5 pIC50 - 1-2,4
pIC50 7.5 [1-2,4]
Retinoid X receptor-α Primary target of this compound Hs Agonist Agonist 7.4 pIC50 - 1-2,4
pIC50 7.4 [1-2,4]
Peroxisome proliferator-activated receptor-γ Hs Antagonist Antagonist ~5.5 pIC50 - 3
pIC50 ~5.5 (IC50 ~3x10-6 M) [3]
Description: Measured using a TR-FRET competitive displacement assay.
Ligand mentioned in the following text fields